From playsuits to black tie with panache, why Sean Connery's Bond will always be the most stylish

Stephen Doig
·3-min read
Bond 
Bond

There’s a reason that, from white tuxedos on Daniel Craig in Spectre  to traditionally English grey three-piece suits on Pierce Brosnan in Goldeneye, every Bond since has paid subtle homage to Connery’s version. Because his was by far the most stylish 007. Of course, it helped that Connery was not just the first cinematic Bond, but so devastatingly handsome with it - the 32 year-old Scotsman made his debut in Dr. No in 1962, his athletic frame the perfect vehicle for the spy’s Savile Row suits. 

The former Edinburgh milkman, who played James Bond until 1971 with a brief reprisal 1983, was able to make the character look at ease both in the princely formalwear that became part of cinematic legend as well as in the breezier, off-duty clothes that formed his tropical wardrobe. In fact, this is where the costume department were able to have the most fun - there aren’t many men who can pull off a baby blue toweling playsuit, as Connery did in 1964’s Goldfinger.

Connery Bond
Connery Bond

It certainly helped that Connery’s olive complexion and dark features looked at home in sun-drenched locations, in a wardrobe that’s as enviable for a summer sojourn today as it was in the 1960. So much so, in fact, that last year British menswear brand Orlebar Brown created a range of holiday-wear inspired by Connery’s Bond lounger looks.

The best of which were Dr. No’s light blue polo and chinos in, matching the azure waters of Jamaica, or louche camp collar shirt in Thunderball. It’s here, coincidentally, that his Bond became an early adopter of teeny-tiny short shorts, some 40 years before Miuccia Prada would propose them for men on her Milan catwalk. 

And while Connery’s Bond acted as a rare example of a British man actually looking sharp in sunny climes, it was back on terra firma that he really cemented the spy’s image as an urbane, pin-sharp assassin-about-town. Marylebone tailor Anthony Sinclair was responsible for creating some of the daytime suiting for Connery’s Bond, be it the classically English 3-piece suit in heavy wools or more corporate single-breasted suits in grey or fawn (which Craig would later nod to in No Time To Die). 

Connery Bond  - Donaldson Collection
Connery Bond - Donaldson Collection

Then there was the eveningwear; every man who slips on a black tie has Connery’s Bond in the back of his mind somewhere. His martini-ready formalwear is, quite simple, the benchmark of after-dark excellence for men. The black tuxedo in Dr. No, with distinctive silk shawl collar, set a high standard, but arguably one that Connery exceeded years later with a white variation in Goldfinger, accessorised with a scarlet flower in his lapel.

Connery Bond
Connery Bond

It helps that, unlike Pierce Brosnan or Roger Moore’s Bond’s (we’ll draw a veil over the unfortunate costume department fripperies of George Lazenby’s version), Sean Connery’s Bond was never beholden to the whim of trends. Blue toweling playsuit aside, there’s a classicism and masculine refinement to his Bond looks that’s timeless. 

Sean Connery’s career was, of course, greater and more varied than just his outing as 007, but it’s in that role that he undoubtedly created a reference point by which men the world over would measure themselves.  An actor's effect on the world of style - or should that be 'shtyle'? - doesn't get more impactful than that. 

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